HCID 178522861, compound → N-(4-Chlorobenzyl)-6-[(1E)-3-hydroxy-1-propenyl]-4-hydroxy-3-quinolinecarboxamide

Participants

Reaction Steps

A mixture of N-(4-chlorobenzyl)-4-hydroxy -6-(3-hydroxy-1-propynyl)-3-quinolinecarboxamide from Preparation No. 5 (5.48 g) and Pd/C (10%, 0.55 g) in 3:1 CH2Cl2/MeOH (150 mL) are placed on a Parr hydrogenator under 50 psi of H2 and shaken for 4 h. Another 0.30 g of Pd/C was added, and the resulting mixture was shaken for 2 h. The reaction mixture is then filtered through Celite, 0.55 g of fresh catalyst is added, and the resulting mixture is shaken under H2 for 3 h. The reaction mixture is then filtered through Celite and concentrated in vacuo. Trituration from CHCl3/MeOH affords a solid which is purified by HPLC chromatography on a 0.46×25 cm Chiralcel OD-H column eluting with EtOH at a rate of 0.3 mL/min to give 0.383 g of N-(4-chlorobenzyl)-1,4-dihydro-6-[(1Z)-3-hydroxy-1-propenyl]-4-oxo-3-quinolinecarboxamide (cis title compound), and 0.492 g of N-(4-chlorobenzyl)-1,4-dihydro-6-[(1E)-3-hydroxy-1-propenyl]-4-oxo-3-quinolinecarboxamide (trans title compound). Crystallization of the cis isomer from ethyl acetate gave 0.29 g of the title cis compound as a solid. Crystallization of the trans isomer from CH2Cl2/MeOH gave 0.289 g of the title trans compound as a solid.

Provenance & Evidence